# Strain‐Sensitive On‐Surface Ladderization by Non‐Dehydrogenative Heterocyclization

https://mdr.nims.go.jp/datasets/8b736c2b-7b65-426f-b17f-cb11ab64dce3

## File

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## Id

8b736c2b-7b65-426f-b17f-cb11ab64dce3

## Local identifier



## Visibility

open_to_public

## State

published

## Created at

2023-12-28T01:38:46.956470Z

## Updated at

2024-01-25T02:15:37.319742Z

## Published at

2024-01-25T03:30:21.277856Z

## Doi

https://doi.org/10.48505/nims.4365

## First published url

https://doi.org/10.1002/chem.202203622

## Date published

2023-03-13

## Recorded date published

2023-3-13

## Resource type

journal_article

## Manuscript type

accepted_manuscript

## Collection



## Title

- title: Strain‐Sensitive On‐Surface Ladderization by Non‐Dehydrogenative Heterocyclization
  title_type: original
  lang: en

## Description

- description: On-surface cyclodehydrogenation recently became an important reaction
    to planarize π-conjugated molecules and oligomers. However, the high-activation
    barrier to cleave the C−H bond often requires high-temperature annealing, consequently
    restricting structures of precursor molecules and/or leading to random fusion
    at their edges. Here, we present a synthesis of pyrrolopyrrole-bridged ladder
    oligomers from 11,11,12,12-tetrabromo-1,4,5,8-tetraaza-9,10-anthraquinodimethane
    molecules on Ag(111) with bond-resolved scanning tunnelling microscopy. This non-dehydrogenative
    cyclization between pyrazine and ethynylene/cumulene groups has a low-activation
    barrier for forming intermediary dimeric oligomer containing dipyrazinopyrrolopyrrolopyrazine
    units, thus giving new insight into the strain-sensitive in ladder-oligomer formation.
  description_type: abstract
  lang: en

## Creator

- name: Yujing Ma
  role: author
  organization: National Institute for Materials Science
- name: Kazuma Sugawara
  role: author
  organization: Hokkaido University
- name: Yusuke Ishigaki
  role: author
  organization: Hokkaido University
- name: Kewei Sun
  role: author
  orcid: https://orcid.org/0000-0002-1835-243X
  organization: National Institute for Materials Science
- name: Takanori Suzuki
  role: author
  organization: Hokkaido University
- name: Shigeki Kawai
  role: author
  orcid: https://orcid.org/0000-0003-2128-0120
  organization: National Institute for Materials Science

## Contact agent



## Publisher

organization: Wiley

## Managing organization



## Keyword

- subject: on-surface ladderization
  schema: not_defined
- subject: non‐dehydrogenative heterocyclization
  schema: not_defined
- subject: strain-sensitive
  schema: not_defined

## Rights

- description: 'This is the peer reviewed version of the following article: Strain‐Sensitive
    On‐Surface Ladderization by Non‐Dehydrogenative Heterocyclization, which has been
    published in final form at https://doi.org/10.1002/chem.202203622. This article
    may be used for non-commercial purposes in accordance with Wiley Terms and Conditions
    for Use of Self-Archived Versions. This article may not be enhanced, enriched
    or otherwise transformed into a derivative work, without express permission from
    Wiley or by statutory rights under applicable legislation. Copyright notices must
    not be removed, obscured or modified. The article must be linked to Wiley’s version
    of record on Wiley Online Library and any embedding, framing or otherwise making
    available the article or pages thereof by third parties from platforms, services
    and websites other than Wiley Online Library must be prohibited.'
  identifier: http://rightsstatements.org/vocab/InC/1.0/

## Other identifier(s)



## Data origin

- data_origin_type: other

## Embargo



## Journal

- title: Chemistry – A European Journal
  issn: '15213765'
  volume: '29'
  issue: '15'
  article_number: e202203622

## Conference



## Related item



## Funding

- identifier: 20H02719
  funder_name: Japan Society for the Promotion of Science
- identifier: 21K18885
  funder_name: Japan Society for the Promotion of Science
- identifier: 21F21058
  funder_name: Japan Society for the Promotion of Science
- identifier: 22H00285
  funder_name: Japan Society for the Promotion of Science
- identifier: 20K21184
  funder_name: Japan Society for the Promotion of Science
- identifier: 21H01912
  funder_name: Japan Society for the Promotion of Science
- identifier: 21H05468
  funder_name: Japan Society for the Promotion of Science

## Instrument



## Instrument operator



## Instrument managing organization



## Measurement method



## Specimen



## Chemical composition



## Structure for specimen



## Structural feature for specimen



## Specific property for specimen



## Process for specimen treatment



## Computational method



## Energy level/transition state



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## Thumbnail

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filename: 20221220 Chem EU Ma_EuroJPhysChem_SI.pdf